1258783-37-7Relevant articles and documents
Trans-tetrahydrofurans by OH-assisted Ru-catalyzed isomerization of 2-butene-1,4-diols
Fehr, Charles,Magpantay, Iris,Saudan, Lionel,Sommer, Horst
, p. 6153 - 6156 (2010)
We herein report a general method for the synthesis of 1,2-annulated trans-tetrahydrofurans by the OH-assisted Ru-catalyzed isomerization of (Z)-2-butene-1,4-diols (using Chaudret's catalyst), followed by reduction of the incipient lactol (using Et3SiH and Amberlyst 15). Alternatively, the lactol can be oxidized to the corresponding lactone (using Ikariya's catalyst). It was shown by labeling experiments that an addition/elimination pathway is (at least to some extent) operative for the isomerization reaction. Only 0.5 mol-% of Chaudret's Ru catalyst is sufficient for the rapid and stereoselective isomerization of enediols of the type shown. This allows ready access to trans-tetrahydrofurans.